So you want to play classic Windows and DOS games on your Mac, but you’re unsure where to begin.

Fortunately, there are quite a few options open to you if you’re craving classics like Thief, Age of Empires 2 and Unreal Tournament but have made the switch to Apple hardware.

Today we’ll be looking at all your available options, and how to choose between them.

But First: The Games Themselves

There’s a good chance you’ve moved on from optical media, particularly if you’re using a MacBook. Apple sells an external optical USB SuperDrive for around $80 which will allow you to use your original media to play games. For quickness you might want to just use disk images though, which contain all the data found on a CD or DVD, as a file stored on your computer.

Half-Life, F-16, Unreal Tournament and Blade Runner are added to my collection. All of them complete in their box! pic.twitter.com/TKfPvqACCk

If you already own the original media, you shouldn’t feel any pangs of guilt by just downloading an .ISO file from a torrent site. This can save you the need to purchase a SuperDrive, as you’d only end up with the same file if you were to extract it yourself.

If you do have a SuperDrive, or you’re using a Mac that is blessed (cursed?) with an optical drive, here’s how to extract a disk image and convert it to .ISO:

1. DOS Emulation & Source Ports

Best for: Old MS-DOS games and golden oldies.

If your games are old enough, you’ll have an easy time getting them to work by way of emulation. Running an app natively on your Mac that’s optimized for your hardware running the game you want to play within it is one of the most stable ways of reliving old games. The one piece of software that has transformed DOS gaming over the last decade or so is DOSBox.

2. Virtualization

Best for: Windows 95, 98 and XP titles, games that use software or hardware rendering.

What better way to run classic Windows than using a native environment? Virtualization allows you to install and run Windows on your Mac, on top of OS X. You’re essentially emulating the hardware and running Windows on top of it. Using specially designed software you can scale your “virtual machines” based on your requirements.

Virtualization does come with a few drawbacks, however. There have been big leaps forward in terms of virtualized 3D graphics performance over the past few years, but you may still encounter compatibility problems like glitches, poor performance and some games refusing to run. It’s also quite draining in terms of processing power and available memory to run two operating systems at once, as you’ll need to provide the VM with a portion of your available power.

For this reason, older versions of Windows (like Windows 98) can run better than modern versions like Windows 7 or 8. MacBook users may also struggle with space allotment, as you’ll need to give your VM some hard drive space to function like a real computer. Lastly, you will need a valid copy of the operating system you’re trying to install.

If you’re keen on going down the virtualization route, you’ll want to use one of these solutions:

VirtualBox is completely free and open source virtualization software from Oracle, available for Windows, Linux, Mac OS X and Solaris. It provides good support for Windows NT 4.0 through to Windows 10 (including XP and 7) but isn’t optimized for Windows 98. You’re going to need to disable hardware acceleration (and use software rendering) or find a third party VESA driver for improved graphical performance.

For that reason VirtualBox is probably best for Windows XP-era games, and those that maintain good compatibility with the Windows 2000-era platform. Think games like Age of Mythology, Call of Dutyand Medal of Honour: Allied Assault. You can also try enabling Microsoft’s own compatibility modes to run Windows 98 and 95-era games by right-clicking the executable file, and choosing Properties.

Fusion is a commercial product from VMWare, and one of the best in terms of 3D performance. Though VirtualBox has improved massively over the last few years, you’ll probably have more luck using Fusion when it comes to compatibility with Windows 98 (installation instructions) and more demanding Windows XP DirectX titles. Best of all you can download a 30-day free trial to see if it does what you need it to.

VMWare make some pretty bold claims on their website, claiming good compatibility with recent versions of DirectX and offering a fusion mode which allows you to run Windows apps in a windowed mode on your Mac desktop. It’s best for games from the Windows XP-era, but you can try Windows 7, and if your hardware can handle it even Windows 8 or 10.

3. Wine

Best for: Some games, but not all — you’ll have to make a call on a game-by-game basis.

Wine, which was initially shorthand for Windows Emulator but now stands for “Wine Is Not an Emulator” is a compatibility layer which allows software written for Windows to run on modern UNIX systems like Linux and Mac OS X. It’s a free, open source project and as such compatibility with software can vary from good to patchy.

As Wine isn’t an emulator, there is no virtualization involved. This means the software places no additional strain on your hardware like VirtualBox or VMWare Fusion will. You don’t have to run two operating systems at once, nor do you have to share processing power or memory with two systems. Unfortunately, as software isn’t running in its native environment, you may encounter issues along the way depending on what you’re trying to run.

Trying Wine for the first time. Installing a Windows app onto a Mac is an eerie feeling!Fingers crossed! pic.twitter.com/cAQF1un5ca

Stability has always been an issue with Wine, whether it’s glitchy graphics, unpredictable behavior, or frequent crashing. You might not be able to get sound working, or network access may be broken, but you can at least consult the WineHQ app database before you try. If you’re serious about using Wine to play games, here’s what you’ll need:

First install the latest version of XQuartz. Even though OS X now comes with XQuartz, the project is updated frequently and the latest version will usually yield the best results. Next download and install Wine for OS X. Once installed, .EXE files will be associated with Wine and you can run them as you would on Windows.

4. Run Windows Natively on Your Mac

Best for: New titles, post-Windows 7 games, and demanding games that require plenty of power to run.

You simply can’t beat running games natively, on an operating system they were designed for, that has full access to your processor, graphics card, and all the RAM you can provide. Boot Camp is Apple’s answer to running Windows on your Mac, and it’s how you’ll get away with playing the latest PC releases on your Apple hardware. Apple even provides all of the drivers you need to get things working — wireless, media keys, touchpads, the lot.

The main drawback here is that you’ll need to reboot your machine from OS X into Windows to play games, as well as sacrificing the hard drive space that Windows requires to function properly (and room for games). If you intend to use Windows on a laptop, you might find that battery life is about half what it is on OS X. Otherwise, Boot Camp provides a great way to use the full potential of your Apple hardware on the latest and greatest titles.

GOG is another online retailer that specializes in classics, hence Good Old Games. Unfortunately, they’re not in the business of porting old Windows titles so most Mac games available either have Mac ports already available, or they’re DOS games that ship with a copy of DOSBox ready to go.

Lastly it’s always worth checking out whether any old Windows games received ports to the Mac. The Mac App Store will often have copies of old Windows games, and the most prolific Mac publisher has to by Aspyr, who have a catalogue of 70+ Mac ports.

Which Will You Choose?

The choice you make here will surely depend on the game in question, the age of your Mac and its hardware, and the operating system which it was initially designed for. Running an app natively is always best — whether that’s a source port, Mac version, emulation via DOSBox, or running your title using Windows via Boot Camp or a virtual machine.

Virtualization is great for those older games that aren’t too demanding, but it might serve you well if you’ve got a recent Mac with an i7 and more RAM than you know what to do with. Provided you can get everything working — sound, 3D acceleration, network access if required — you’ll have a stable experience and you won’t have to reboot your system.

Choose Wine if the game in question is well-supported, or you’re having trouble going down the virtual machine route. For modern games, you’ll want to use Boot Camp to install Windows alongside OS X to take full advantage of your device’s hardware.

Which old Windows or DOS games will you be playing on your Mac? Let’s get all nostalgic in the comments, below.